WO2021244951A1 - Fungicidal compositions - Google Patents

Fungicidal compositions Download PDF

Info

Publication number
WO2021244951A1
WO2021244951A1 PCT/EP2021/064261 EP2021064261W WO2021244951A1 WO 2021244951 A1 WO2021244951 A1 WO 2021244951A1 EP 2021064261 W EP2021064261 W EP 2021064261W WO 2021244951 A1 WO2021244951 A1 WO 2021244951A1
Authority
WO
WIPO (PCT)
Prior art keywords
methyl
difluoro
pyridyl
compound
amino
Prior art date
Application number
PCT/EP2021/064261
Other languages
French (fr)
Other versions
WO2021244951A9 (en
Inventor
David Burns
Mattia Riccardo MONACO
Stefano RENDINE
Clemens Lamberth
Mathias Blum
Andrew Edmunds
Original Assignee
Syngenta Crop Protection Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to CA3178082A priority Critical patent/CA3178082A1/en
Priority to KR1020227044991A priority patent/KR20230019126A/en
Priority to EP21728570.9A priority patent/EP4161277A1/en
Priority to US18/000,014 priority patent/US20230270114A1/en
Priority to CR20220616A priority patent/CR20220616A/en
Priority to CN202180040155.6A priority patent/CN115697063A/en
Priority to AU2021284956A priority patent/AU2021284956A1/en
Priority to MX2022015065A priority patent/MX2022015065A/en
Application filed by Syngenta Crop Protection Ag filed Critical Syngenta Crop Protection Ag
Priority to JP2022574142A priority patent/JP2023527894A/en
Priority to BR112022024658A priority patent/BR112022024658A2/en
Priority to IL298217A priority patent/IL298217A/en
Publication of WO2021244951A1 publication Critical patent/WO2021244951A1/en
Publication of WO2021244951A9 publication Critical patent/WO2021244951A9/en
Priority to CONC2022/0016858A priority patent/CO2022016858A2/en

Links

Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/06Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/781,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01PBIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00Fungicides
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N2300/00Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48

Definitions

  • the present invention relates to novel fungicidal compositions, to their use in agriculture or horticulture for controlling diseases caused by phytopathogens, especially phytopathogenic fungi, and to methods of controlling diseases on useful plants.
  • WO 2010/012793, WO 2017/207362, and WO 2019/105933 describe thiazole derivatives as pesticidal agents. Whilst many fungicidal compounds and compositions, belonging to various different chemical classes, have been/are being developed for use as fungicides in crops of useful plants, crop tolerance and activity against particular phytopathogenic fungi do not always satisfy the needs of agricultural practice in many respects.
  • compositions comprising mixtures of different fungicidal compounds possessing different modes of action can address some of these needs (e.g., by combining fungicides with differing spectrums of activity).
  • component (A) is a compound of formula (I): wherein X is N; Y is C-F or C-H; R 1 is hydrogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, C 1 -C 3 hydroxyalkyl, C 1 -C 3 alkoxyC 1 - C4alkyl, C 3 -C 4 cycloalkyl, C 1 -C 2 alkoxyC 1 -C 2 alkoxy, C 1 -C 3 alkoxycarbonylC 1 -C 3 alkyl, C 1 - C 2 alkoxycarbonyloxy
  • the weight ratio of component (A) to component (B) may preferably be from 100:1 to 1:100, from 50:1 to 1:50, from 20:1 to 1:40, from 15:1 to 1:30, from 12:1 to 1:25, from 10:1 to 1:20, from 5:1 and 1:15, from 3:1 to 1:10 or from 2:1 to 1:5.
  • a method of controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi, on useful plants or on propagation material thereof which comprises applying to the useful plants, the locus thereof or propagation material thereof a fungicidal composition according to the invention.
  • fungicidal mixture compositions according to the invention may also include, inter alia, advantageous levels of biological activity for protecting plants against diseases that are caused by fungi or superior properties for use as agrochemical active ingredients (for example, greater biological activity, an advantageous spectrum of activity, an increased safety profile, improved physico-chemical properties, or increased biodegradability).
  • advantageous levels of biological activity for protecting plants against diseases that are caused by fungi or superior properties for use as agrochemical active ingredients for example, greater biological activity, an advantageous spectrum of activity, an increased safety profile, improved physico-chemical properties, or increased biodegradability.
  • the presence of one or more possible asymmetric carbon atoms in a compound of formula (I) means that the compounds may occur in optically isomeric forms, i.e., enantiomeric or diastereomeric forms. Also atropisomers may occur as a result of restricted rotation about a single bond.
  • the present invention includes all those possible isomeric forms (e.g.
  • the present invention includes all possible tautomeric forms for a compound of formula (I), and also a racemic compound, i.e., a mixture of at least two enantiomers in a ratio of substantially 50:50.
  • the compounds of formula (I) according to the invention are in free form, in oxidized form as a N-oxide or in salt form, e.g. an agronomically usable salt form.
  • N-oxides are oxidized forms of tertiary amines or oxidized forms of nitrogen containing heteroaromatic compounds. They are described for instance in the book “Heterocyclic N-oxides” by A. Albini and S.
  • Y is C-F or C-H. In one set of embodiments, Y is C-F. In another set of embodiments, Y is C-H.
  • X is N.
  • R 1 is hydrogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, C 1 -C 3 hydroxyalkyl, C 1 -C 3 alkoxy C 1 - C4alkyl, C 3 -C 4 cycloalkyl, C 1 -C 2 alkoxyC 1 -C 2 alkoxy, C 1 -C 3 alkoxycarbonylC 1 -C 3 alkyl, C 1 - C 2 alkoxycarbonyloxyC 1 -C 2 alkyl, C 1 -C 2 alkycarbonyloxyC 1 -C 2 alkyl, C 3 -C 4 alkynyloxy, C 1 -C 3 alkylsulfanyl, diethylamino, phenyl, benzyl, phenoxy, benzyloxyC 1 -C 2 alkyl, thienyl, or furanyl.
  • R 1 is hydrogen, methyl, ethyl, isopropyl, methoxy, ethoxy, fluoromethyl, chloromethyl, bromomethyl, 2,2,2-trifuoroethyl, 1-hydroxyethyl, methoxymethyl, 1-methoxyethyl, 1-ethoxymethyl, 1- methoxy-1-methylethyl, cyclopropyl, methoxyethoxy, ethoxycarbonyl, 2-methoxy-2-oxo-ethyl, 2- methoxy-oxo-ethyl, 2-methoxy-oxo-propyl, propargyloxy, 1-methoxycarbonyloxy-ethyl, 1- ethoxycarbonyloxy-ethyl, 1-methylcarbonyloxy-ethyl, methylcarbonyloxymethyl, methylsulfanyl, ethylsulfanyl, isopropylsulfanyl, diethylamino,
  • R 1 is hydrogen, methyl, ethyl, isopropyl, methoxy, ethoxy, fluoromethyl, 2,2,2- trifuoroethyl, 1-hydroxyethyl, 1-ethoxymethyl, cyclopropyl, methoxyethoxy, 2-methoxy-2-oxo-ethyl, 2- methoxy-oxo-ethyl, 2-methoxy-oxo-propyl, propargyloxy, 1-methoxycarbonyloxy-ethyl, 1- ethoxycarbonyloxy-ethyl, 1-methylcarbonyloxy-ethyl, methylcarbonyloxymethyl, isopropylsulfanyl, diethylamino, phenyl, benzyl, phenoxy, benzyloxymethyl, 1-benzyloxyethyl, 2-furanyl, or 2-thiophenyl.
  • R 2 is C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl or HC(O)NH-.
  • R 1 is C 1 -C 3 alkyl or C 1 - C3alkoxy. More preferably, R 1 is methyl or methoxy.
  • R 3 is C3-C6cycloalkyl, wherein the cycloalkyl groups are optionally substituted with 1 or 2 groups represented by R 4 , or R 3 is a 6- to 10-membered non-aromatic spirocyclic carbobi-cyclyl ring system.
  • R 3 is C 3 -C 4 cycloalkyl, wherein the cycloalkyl groups are optionally substituted with 1 or 2 groups represented by R 4 , or R 3 is a 6- to 8-membered non-aromatic spirocyclic carbobi-cyclyl ring system. More preferably, R 3 is cyclobutyl, 2,2-dimethylcyclobutyl or spiro[3.4]octanyl, and most preferably, cyclobutyl, 2,2-dimethylcyclobutyl, or spiro[3.4]octan-3-yl. R 4 is C 1 -C 3 alkyl.
  • R 4 is methyl, ethyl or isopropyl. More preferably, R 4 is methyl.
  • component (A) is a compound selected from: [2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1- methyl-2-oxo-ethyl] acetate (compound X.01); [2-[[4-(cyclobutylcarbamoyl)-5-methyl-thiazol-2-yl]-(2,6-difluoro-4-pyridyl)amino]-1-methyl-2-oxo- ethyl] ethyl carbonate (compound X.02); [2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan
  • component (A) is a compound selected from: [2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1- methyl-2-oxo-ethyl] acetate (compound X.01); [2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1- methyl-2-oxo-ethyl] ethyl carbonate (compound X.04); N-cyclobutyl-2-[(2,6-difluoro-4-pyridyl)-(2-methoxypropanoyl)amino]-5-methyl-thiazole-4- carboxamide (compound X.07
  • component (A) is a compound selected from: [2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1- methyl-2-oxo-ethyl] acetate (compound X.01); [2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1- methyl-2-oxo-ethyl] ethyl carbonate (compound X.04); 2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-5-methyl-N-spiro[3.4]octan-3-yl-thiazole-4- car
  • component (A) is a compound selected from: [2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1- methyl-2-oxo-ethyl] acetate (compound X.01); 2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-5-methyl-N-spiro[3.4]octan-3-yl-thiazole-4- carboxamide (compound X.11); N-cyclobutyl-2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-5-methyl-thiazole-4- carboxamide (compound X.12); 2-[acetyl-(2,6-difluoro-4-pyridyl
  • component (B) is a compound selected from the group consisting of: azoxystrobin, trifloxystrobin, pyraclostrobin, picoxystrobin, coumoxystrobin, metyltetraprole, cyproconazole, tebuconazole, difenoconazole, hexaconazole, propiconazole, fenhexamid, prothioconazole, mefentrifluconazole, prochloraz, fenpropidin, fenpropimorph, fluxapyroxad, fluopyram, isopyrazam, sedaxane, benzovindiflupyr, pydiflumetofen, isoflucypram, bixafen, penthiopyrad, inpyrfluxam, isofetamid, pyrapropoyne, fluindapyr, fenpicoxamid, florylpicoxamid, aci
  • component (B) is selected from the group consisting of: azoxystrobin, trifloxystrobin, pyraclostrobin, picoxystrobin, coumoxystrobin, metyltetraprole, cyproconazole, tebuconazole, difenoconazole, hexaconazole, propiconazole, fenhexamid, prothioconazole, mefentrifluconazole, prochloraz, fenpropidin, fenpropimorph, fluxapyroxad, fluopyram, isopyrazam, sedaxane, benzovindiflupyr, pydiflumetofen, isoflucypram, bixafen, penthiopyrad, inpyrfluxam, isofetamid, pyrapropoyne, fluindapyr, fenpicoxamid, florylpicoxamid, acibenzolar-
  • component (B) is a compound selected from the group consisting of: azoxystrobin, trifloxystrobin, metyltetraprole, difenoconazole, hexaconazole, propiconazole, prothioconazole, mefentrifluconazole, fenpropidin, fenpropimorph, fluxapyroxad, fluopyram, isopyrazam, sedaxane, benzovindiflupyr, pydiflumetofen, isoflucypram, isofetamid, pyrapropoyne, fluindapyr, fenpicoxamid, florylpicoxamid, acibenzolar-S-methyl, chlorothalonil, mancozeb, mandipropamid, oxathiapiprolin, fluazinam, fludioxonil, cyprodinil, metalaxyl-M, aminopyrifen, fol
  • Example B10 Sclerotinia sclerotiorum / liquid culture (cottony rot) Mycelia fragments of a newly grown liquid culture of the fungus are directly mixed into nutrient broth (Vogel’s minimal media) containing 200 ⁇ Mol SHAM. After placing a (DMSO) solution of test compounds into a microtiter plate (96-well format) the nutrient broth containing the fungal material is added. The test plates are incubated at 24 °C and the inhibition of growth is determined photometrically 3-4 days after application. The following mixture compositions (A:B) at the reported concentration (in ppm) gave at least 80% disease control in this test when compared to the untreated control under the same conditions, which showed extensive disease development.
  • DMSO DMSO
  • Example B11 Blumeria graminis f. sp. tritici (Erysiphe graminis f. sp. tritici) / wheat / leaf disc preventative (Powdery mildew on wheat)
  • Wheat leaf segments cv. Kanzler are placed on agar in a multiwell plate (24-well format) and sprayed with the formulated test compounds diluted in water. The leaf disks are inoculated by shaking powdery mildew infected plants above the test plates 1 day after application.
  • the inoculated leaf disks are incubated at 20 °C and 60% rh under a light regime of 24 h darkness followed by 12 h light / 12 h darkness in a climate chamber and the activity of the compounds is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears on untreated check leaf segments (6 - 8 days after application).
  • the following mixture compositions (A:B) at the reported concentration (in ppm) gave at least 80% disease control in this test when compared to the untreated control under the same conditions, which showed extensive disease development.
  • Example B12 Puccinia recondita f. sp. tritici / wheat / leaf disc preventative (Brown rust) Wheat leaf segments cv. Kanzler are placed on agar in multiwell plates (24-well format) and sprayed with the formulated test compounds diluted in water. The leaf disks are inoculated with a spore suspension of the fungus 1 day after application. The inoculated leaf segments are incubated at 19 °C and 75% rh under a light regime of 12 h light / 12 h darkness in a climate cabinet and the activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (7 - 9 days after application).

Abstract

A fungicidal composition comprising a mixture of components (A) and (B), wherein components (A) and (B) are as defined in claim 1, and use of the compositions in agriculture or horticulture for controlling or preventing infestation of plants by phytopathogenic microorganisms, preferably fungi.

Description

FUNGICIDAL COMPOSITIONS The present invention relates to novel fungicidal compositions, to their use in agriculture or horticulture for controlling diseases caused by phytopathogens, especially phytopathogenic fungi, and to methods of controlling diseases on useful plants. WO 2010/012793, WO 2017/207362, and WO 2019/105933 describe thiazole derivatives as pesticidal agents. Whilst many fungicidal compounds and compositions, belonging to various different chemical classes, have been/are being developed for use as fungicides in crops of useful plants, crop tolerance and activity against particular phytopathogenic fungi do not always satisfy the needs of agricultural practice in many respects. Therefore, there is a continuing need to find new compounds and compositions having superior biological properties for use in controlling or preventing infestation of plants by phytopathogenic fungi. For example, compounds possessing a greater biological activity, an advantageous spectrum of activity, an increased safety profile, improved physico-chemical properties, increased biodegradability. Or else, compositions possessing a broader spectrum of activity, improved crop tolerance, synergistic interactions or potentiating properties, or compositions which display a more rapid onset of action or which have longer lasting residual activity or which enable a reduction in the number of applications and/or a reduction in the application rate of the compounds and compositions required for effective control of a phytopathogen, thereby enabling beneficial resistance-management practices, reduced environmental impact and reduced operator exposure. The use of compositions comprising mixtures of different fungicidal compounds possessing different modes of action can address some of these needs (e.g., by combining fungicides with differing spectrums of activity). According to the present invention, there is provided a fungicidal composition comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is a compound of formula (I): wherein
Figure imgf000002_0001
X is N; Y is C-F or C-H; R1 is hydrogen, C1-C3alkyl, C1-C3alkoxy, C1-C3haloalkyl, C1-C3hydroxyalkyl, C1-C3alkoxyC1- C4alkyl, C3-C4cycloalkyl, C1-C2alkoxyC1-C2alkoxy, C1-C3alkoxycarbonylC1-C3alkyl, C1- C2alkoxycarbonyloxyC1-C2alkyl, C1-C2alkycarbonyloxyC1-C2alkyl, C3-C4alkynyloxy, C1-C3alkylsulfanyl, diethylamino, phenyl, benzyl, phenoxy, benzyloxyC1-C2alkyl, thienyl, or furanyl; R2 is C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkyl or HC(O)NH-; R3 is C3-C6cycloalkyl, wherein the cycloalkyl groups are optionally substituted with 1 or 2 groups represented by R4, or R3 is a 6- to 10-membered non-aromatic spirocyclic carbobi-cyclyl ring system; R4 is C1-C3alkyl; or a salt or an N-oxide thereof; and component (B) is a compound selected from the group consisting of: azoxystrobin, trifloxystrobin, pyraclostrobin, picoxystrobin, coumoxystrobin, metyltetraprole, cyproconazole, tebuconazole, difenoconazole, hexaconazole, propiconazole, fenhexamid, prothioconazole, mefentrifluconazole, prochloraz, fenpropidin, fenpropimorph, fluxapyroxad, fluopyram, isopyrazam, sedaxane, benzovindiflupyr, pydiflumetofen, isoflucypram, bixafen, penthiopyrad, inpyrfluxam, isofetamid, pyrapropoyne, fluindapyr, fenpicoxamid, florylpicoxamid, acibenzolar-S-methyl, trinexepac-ethyl, fosetyl-aluminium, chlorothalonil, mancozeb, mandipropamid, oxathiapiprolin, fluazinam, fludioxonil, cyprodinil, metalaxyl-M, aminopyrifen, folpet, ipflufenoquin, quinofumelin, tebufloquin, tolprocarb, tricyclazole, pyroquilon, cyflufenamid, metrafenone, N'-[2-chloro-4-(2- fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine, (this compound may be prepared from the methods described in WO 2016/202742); N'-[4-(2-bromophenoxy)-5-chloro-2-methyl-phenyl]-N- ethyl-N-methyl-formamidine, (this compound may be prepared from the methods described in WO 2016/202688); N-(1-benzyl-1,3-dimethyl-butyl)-8-fluoro-quinoline-3-carboxamide, N-(1-benzyl-3,3,3- trifluoro-1-methyl-propyl)-8-fluoro-quinoline-3-carboxamide, N-(1-benzyl-3-chloro-1-methyl-but-3-enyl)- 8-fluoro-quinoline-3-carboxamide, (these compounds may be prepared from the methods described in WO 2017/153380); 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 1-(6,7- dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline, (these compounds may be prepared from the methods described in WO 2017/025510); 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5- trifluoro-3,3-dimethyl-isoquinoline, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl- isoquinoline, 6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline, (these compounds may be prepared from the methods described in WO 2016/156085); N'-[5-bromo-2-methyl- 6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-chloro-2-methyl-6-(1- methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(1-methyl- 2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine, (these compounds may be prepared from the methods described in WO 2015/155075); N-isopropyl-N’-[5-methoxy-2-methyl-4-(2,2,2- trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidine, (this compound may be prepared from the methods described in WO 2018/228896); N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, ethyl 1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3-amine, (these compounds may be prepared from the methods described in WO 2017/055473, WO 2017/055469, WO 2017/093348 and WO 2017/118689); methyl (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazol-1-yl]phenoxy]prop- 2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazol-1-yl)phenoxy]prop-2-enoate, methyl (Z)-2-[5-(3-isopropylpyrazol-1-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-3-methoxy- 2-[2-methyl-5-(4-propyltriazol-2-yl)phenoxy]prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-[4- (trifluoromethyl)triazol-2-yl]phenoxy]prop-2-enoate, (these compounds may be prepared from the methods described in WO 2020/079111); methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy- prop-2-enoate, methyl (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, methyl (Z)-2- [5-(4-cyclohexylthiazol-2-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-2-[5-[4- (ethoxymethyl)thiazol-2-yl]-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-2-[5-(4- bromothiazol-2-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5- [5-(trifluoromethyl)thiazol-2-yl]phenoxy]prop-2-enoate, TAEGRO® (i.e, Bacillus amyloliquefaciens strain FZB24), Timorex GoldTM (plant extract comprising tea tree oil), and metarylpicoxamid. In general, the weight ratio of component (A) to component (B) may preferably be from 100:1 to 1:100, from 50:1 to 1:50, from 20:1 to 1:40, from 15:1 to 1:30, from 12:1 to 1:25, from 10:1 to 1:20, from 5:1 and 1:15, from 3:1 to 1:10 or from 2:1 to 1:5. Further according to the invention, there is provided a method of controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi, on useful plants or on propagation material thereof, which comprises applying to the useful plants, the locus thereof or propagation material thereof a fungicidal composition according to the invention. The benefits provided by certain fungicidal mixture compositions according to the invention may also include, inter alia, advantageous levels of biological activity for protecting plants against diseases that are caused by fungi or superior properties for use as agrochemical active ingredients (for example, greater biological activity, an advantageous spectrum of activity, an increased safety profile, improved physico-chemical properties, or increased biodegradability). The presence of one or more possible asymmetric carbon atoms in a compound of formula (I) means that the compounds may occur in optically isomeric forms, i.e., enantiomeric or diastereomeric forms. Also atropisomers may occur as a result of restricted rotation about a single bond. The present invention includes all those possible isomeric forms (e.g. geometric isomers) and mixtures thereof for a compound of formula (I). The present invention includes all possible tautomeric forms for a compound of formula (I), and also a racemic compound, i.e., a mixture of at least two enantiomers in a ratio of substantially 50:50. In each case, the compounds of formula (I) according to the invention are in free form, in oxidized form as a N-oxide or in salt form, e.g. an agronomically usable salt form. N-oxides are oxidized forms of tertiary amines or oxidized forms of nitrogen containing heteroaromatic compounds. They are described for instance in the book “Heterocyclic N-oxides” by A. Albini and S. Pietra, CRC Press, Boca Raton 1991. Preferred groups and values for the substituents in the compounds of formula (I) are, in any combination thereof, as set out below. Y is C-F or C-H. In one set of embodiments, Y is C-F. In another set of embodiments, Y is C-H. X is N. R1 is hydrogen, C1-C3alkyl, C1-C3alkoxy, C1-C3haloalkyl, C1-C3hydroxyalkyl, C1-C3alkoxy C1- C4alkyl, C3-C4cycloalkyl, C1-C2alkoxyC1-C2alkoxy, C1-C3alkoxycarbonylC1-C3alkyl, C1- C2alkoxycarbonyloxyC1-C2alkyl, C1-C2alkycarbonyloxyC1-C2alkyl, C3-C4alkynyloxy, C1-C3alkylsulfanyl, diethylamino, phenyl, benzyl, phenoxy, benzyloxyC1-C2alkyl, thienyl, or furanyl. Preferably, R1 is hydrogen, methyl, ethyl, isopropyl, methoxy, ethoxy, fluoromethyl, chloromethyl, bromomethyl, 2,2,2-trifuoroethyl, 1-hydroxyethyl, methoxymethyl, 1-methoxyethyl, 1-ethoxymethyl, 1- methoxy-1-methylethyl, cyclopropyl, methoxyethoxy, ethoxycarbonyl, 2-methoxy-2-oxo-ethyl, 2- methoxy-oxo-ethyl, 2-methoxy-oxo-propyl, propargyloxy, 1-methoxycarbonyloxy-ethyl, 1- ethoxycarbonyloxy-ethyl, 1-methylcarbonyloxy-ethyl, methylcarbonyloxymethyl, methylsulfanyl, ethylsulfanyl, isopropylsulfanyl, diethylamino, phenyl, benzyl, phenoxy, benzyloxymethyl, 1- benzyloxyethyl, 2-furanyl, or 2-thiophenyl. More preferably, R1 is hydrogen, methyl, ethyl, isopropyl, methoxy, ethoxy, fluoromethyl, 2,2,2- trifuoroethyl, 1-hydroxyethyl, 1-ethoxymethyl, cyclopropyl, methoxyethoxy, 2-methoxy-2-oxo-ethyl, 2- methoxy-oxo-ethyl, 2-methoxy-oxo-propyl, propargyloxy, 1-methoxycarbonyloxy-ethyl, 1- ethoxycarbonyloxy-ethyl, 1-methylcarbonyloxy-ethyl, methylcarbonyloxymethyl, isopropylsulfanyl, diethylamino, phenyl, benzyl, phenoxy, benzyloxymethyl, 1-benzyloxyethyl, 2-furanyl, or 2-thiophenyl. R2 is C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkyl or HC(O)NH-. Preferably, R1 is C1-C3alkyl or C1- C3alkoxy. More preferably, R1 is methyl or methoxy. R3 is C3-C6cycloalkyl, wherein the cycloalkyl groups are optionally substituted with 1 or 2 groups represented by R4, or R3 is a 6- to 10-membered non-aromatic spirocyclic carbobi-cyclyl ring system. Preferably, R3 is C3-C4cycloalkyl, wherein the cycloalkyl groups are optionally substituted with 1 or 2 groups represented by R4, or R3 is a 6- to 8-membered non-aromatic spirocyclic carbobi-cyclyl ring system. More preferably, R3 is cyclobutyl, 2,2-dimethylcyclobutyl or spiro[3.4]octanyl, and most preferably, cyclobutyl, 2,2-dimethylcyclobutyl, or spiro[3.4]octan-3-yl. R4 is C1-C3alkyl. Preferably, R4 is methyl, ethyl or isopropyl. More preferably, R4 is methyl. Preferably, component (A) is a compound selected from: [2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1- methyl-2-oxo-ethyl] acetate (compound X.01); [2-[[4-(cyclobutylcarbamoyl)-5-methyl-thiazol-2-yl]-(2,6-difluoro-4-pyridyl)amino]-1-methyl-2-oxo- ethyl] ethyl carbonate (compound X.02); [2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1- methyl-2-oxo-ethyl] methyl carbonate (compound X.03); [2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1- methyl-2-oxo-ethyl] ethyl carbonate (compound X.04); 2-[(2,6-difluoro-4-pyridyl)-(2-hydroxypropanoyl)amino]-5-methyl-N-spiro[3.4]octan-3-yl-thiazole- 4-carboxamide (compound X.05); 2-[2-benzyloxypropanoyl-(2,6-difluoro-4-pyridyl)amino]-N-cyclobutyl-5-methyl-thiazole-4- carboxamide (compound X.06); N-cyclobutyl-2-[(2,6-difluoro-4-pyridyl)-(2-methoxypropanoyl)amino]-5-methyl-thiazole-4- carboxamide (compound X.07); [2-[(2,6-difluoro-4-pyridyl)-[4-[(2,2-dimethylcyclobutyl)carbamoyl]-5-methyl-thiazol-2-yl]amino]-2- oxo-ethyl] acetate (compound X.08); 2-[(2,6-difluoro-4-pyridyl)-(2-phenylacetyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.09); 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-5-methoxy-N-spiro[3.4]octan-3-yl-thiazole-4-carboxamide (compound X.10); 2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-5-methyl-N-spiro[3.4]octan-3-yl-thiazole-4- carboxamide (compound X.11); N-cyclobutyl-2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-5-methyl-thiazole-4- carboxamide (compound X.12); 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-N-cyclobutyl-5-methyl-thiazole-4-carboxamide (compound X.13); 2-[(2-benzyloxyacetyl)-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl- thiazole-4-carboxamide (compound X.14); 2-[(2,6-difluoro-4-pyridyl)-(2-ethoxyacetyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.15); 2-[diethylcarbamoyl-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole- 4-carboxamide (compound X.16); 2-[(2-chloroacetyl)-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.17); methyl 3-[(2,6-difluoro-4-pyridyl)-[4-[(2,2-dimethyl cyclobutyl)carbamoyl]-5-methyl-thiazol-2- yl]amino]-3-oxo-propanoate (compound X.18); 2-[(2,6-difluoro-4-pyridyl)-(furan-2-carbonyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl- thiazole-4-carboxamide (compound X.19); methyl 5-[(2,6-difluoro-4-pyridyl)-[4-[(2,2-dimethyl cyclobutyl)carbamoyl]-5-methyl-thiazol-2-yl] amino]-5-oxo-pentanoate (compound X.20); 2-[(2,6-difluoro-4-pyridyl)-(3,3,3-trifluoropropanoyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl- thiazole-4-carboxamide (compound X.21); S-isopropyl N-(2,6-difluoro-4-pyridyl)-N-[4-[(2,2-dimethyl cyclobutyl)carbamoyl]-5-methyl-thiazol- 2-yl]carbamothioate (compound X.22); methyl 4-[(2,6-difluoro-4-pyridyl)-[4-[(2,2-dimethyl cyclobutyl)carbamoyl]-5-methyl-thiazol-2- yl]amino]-4-oxo-butanoate (compound X.23); 2-[cyclopropane carbonyl-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl- thiazole-4-carboxamide (compound X.24); 2-[cyclopropane carbonyl-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl- thiazole-4-carboxamide (compound X.25); phenyl N-(2,6-difluoro-4-pyridyl)-N-[4-[(2,2-dimethylcyclobutyl)carbamoyl]-5-methyl-thiazol-2- yl]carbamate (compound X.26); 2-[(2,6-difluoro-4-pyridyl)-(2-fluoroacetyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.27); 2-methoxyethyl N-(2,6-difluoro-4-pyridyl)-N-[4-[(2,2-dimethylcyclobutyl)carbamoyl]-5-methyl- thiazol-2-yl]carbamate (compound X.28); 2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl- thiazole-4-carboxamide (compound X.29); ethyl N-(2,6-difluoro-4-pyridyl)-N-[4-[(2,2-dimethylcyclobutyl)carbamoyl]-5-methyl-thiazol-2- yl]carbamate (compound X.30); 2-[(2,6-difluoro-4-pyridyl)-(thiophene-2-carbonyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl- thiazole-4-carboxamide (compound X.31); methyl N-(2,6-difluoro-4-pyridyl)-N-[4-[(2,2-dimethylcyclobutyl)carbamoyl]-5-methyl-thiazol-2- yl]carbamate (compound X.32); 2-[(2,6-difluoro-4-pyridyl)-formyl-amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.33); ethyl 2-[(2,6-difluoro-4-pyridyl)-[4-[(2,2-dimethylcyclobutyl)carbamoyl]-5-methyl-thiazol-2- yl]amino]-2-oxo-acetate (compound X.34); 2-[benzoyl-(2,6-difluoro-4-pyridyl) amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.35); 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.36); 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-5-methyl-N-spiro[3.4] octan-3-yl-thiazole-4-carboxamide (compound X.37); and 2-[(2,6-difluoro-4-pyridyl)-(2-methylpropanoyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl- thiazole-4-carboxamide (X.38). More preferably, component (A) is a compound selected from: [2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1- methyl-2-oxo-ethyl] acetate (compound X.01); [2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1- methyl-2-oxo-ethyl] ethyl carbonate (compound X.04); N-cyclobutyl-2-[(2,6-difluoro-4-pyridyl)-(2-methoxypropanoyl)amino]-5-methyl-thiazole-4- carboxamide (compound X.07); 2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-5-methyl-N-spiro[3.4]octan-3-yl-thiazole-4- carboxamide (compound X.11); N-cyclobutyl-2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-5-methyl-thiazole-4- carboxamide (compound X.12); 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-N-cyclobutyl-5-methyl-thiazole-4-carboxamide (compound X.13); 2-[(2-benzyloxyacetyl)-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl- thiazole-4-carboxamide (compound X.14); 2-[(2-chloroacetyl)-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.17); methyl 3-[(2,6-difluoro-4-pyridyl)-[4-[(2,2-dimethyl cyclobutyl)carbamoyl]-5-methyl-thiazol-2- yl]amino]-3-oxo-propanoate (compound X.18); 2-[(2,6-difluoro-4-pyridyl)-(furan-2-carbonyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl- thiazole-4-carboxamide (compound X.19); S-isopropyl N-(2,6-difluoro-4-pyridyl)-N-[4-[(2,2-dimethyl cyclobutyl)carbamoyl]-5-methyl-thiazol- 2-yl]carbamothioate (compound X.22); 2-[cyclopropane carbonyl-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl- thiazole-4-carboxamide (compound X.24); phenyl N-(2,6-difluoro-4-pyridyl)-N-[4-[(2,2-dimethylcyclobutyl)carbamoyl]-5-methyl-thiazol-2- yl]carbamate (compound X.26); 2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl- thiazole-4-carboxamide (compound X.29); 2-[(2,6-difluoro-4-pyridyl)-(thiophene-2-carbonyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl- thiazole-4-carboxamide (compound X.31); 2-[(2,6-difluoro-4-pyridyl)-formyl-amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.33); ethyl 2-[(2,6-difluoro-4-pyridyl)-[4-[(2,2-dimethylcyclobutyl)carbamoyl]-5-methyl-thiazol-2- yl]amino]-2-oxo-acetate (compound X.34); 2-[benzoyl-(2,6-difluoro-4-pyridyl) amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.35); 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.36); 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-5-methyl-N-spiro[3.4] octan-3-yl-thiazole-4-carboxamide (compound X.37); and 2-[(2,6-difluoro-4-pyridyl)-(2-methylpropanoyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl- thiazole-4-carboxamide (X.38). Even more preferably, component (A) is a compound selected from: [2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1- methyl-2-oxo-ethyl] acetate (compound X.01); [2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1- methyl-2-oxo-ethyl] ethyl carbonate (compound X.04); 2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-5-methyl-N-spiro[3.4]octan-3-yl-thiazole-4- carboxamide (compound X.11); N-cyclobutyl-2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-5-methyl-thiazole-4- carboxamide (compound X.12); 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-N-cyclobutyl-5-methyl-thiazole-4-carboxamide (compound X.13); 2-[(2-chloroacetyl)-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.17); methyl 3-[(2,6-difluoro-4-pyridyl)-[4-[(2,2-dimethyl cyclobutyl)carbamoyl]-5-methyl-thiazol-2- yl]amino]-3-oxo-propanoate (compound X.18); 2-[(2,6-difluoro-4-pyridyl)-(furan-2-carbonyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl- thiazole-4-carboxamide (compound X.19); 2-[cyclopropane carbonyl-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl- thiazole-4-carboxamide (compound X.24); 2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl- thiazole-4-carboxamide (compound X.29); 2-[(2,6-difluoro-4-pyridyl)-formyl-amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.33); ethyl 2-[(2,6-difluoro-4-pyridyl)-[4-[(2,2-dimethylcyclobutyl)carbamoyl]-5-methyl-thiazol-2- yl]amino]-2-oxo-acetate (compound X.34); 2-[benzoyl-(2,6-difluoro-4-pyridyl) amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.35); 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.36); 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-5-methyl-N-spiro[3.4] octan-3-yl-thiazole-4-carboxamide (compound X.37); and 2-[(2,6-difluoro-4-pyridyl)-(2-methylpropanoyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl- thiazole-4-carboxamide (X.38). More preferably still, component (A) is a compound selected from: [2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1- methyl-2-oxo-ethyl] acetate (compound X.01); 2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-5-methyl-N-spiro[3.4]octan-3-yl-thiazole-4- carboxamide (compound X.11); N-cyclobutyl-2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-5-methyl-thiazole-4- carboxamide (compound X.12); 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-N-cyclobutyl-5-methyl-thiazole-4-carboxamide (compound X.13); 2-[(2,6-difluoro-4-pyridyl)-(furan-2-carbonyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl- thiazole-4-carboxamide (compound X.19); 2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl- thiazole-4-carboxamide (compound X.29); 2-[(2,6-difluoro-4-pyridyl)-formyl-amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.33); 2-[benzoyl-(2,6-difluoro-4-pyridyl) amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.35); 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.36); 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-5-methyl-N-spiro[3.4] octan-3-yl-thiazole-4-carboxamide (compound X.37); and 2-[(2,6-difluoro-4-pyridyl)-(2-methylpropanoyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl- thiazole-4-carboxamide (X.38). Table X
Figure imgf000010_0001
Figure imgf000011_0001
Figure imgf000012_0001
Figure imgf000013_0001
Figure imgf000014_0001
Figure imgf000015_0001
Figure imgf000016_0001
Figure imgf000017_0001
Preferably, component (B) is a compound selected from the group consisting of: azoxystrobin, trifloxystrobin, pyraclostrobin, picoxystrobin, coumoxystrobin, metyltetraprole, cyproconazole, tebuconazole, difenoconazole, hexaconazole, propiconazole, fenhexamid, prothioconazole, mefentrifluconazole, prochloraz, fenpropidin, fenpropimorph, fluxapyroxad, fluopyram, isopyrazam, sedaxane, benzovindiflupyr, pydiflumetofen, isoflucypram, bixafen, penthiopyrad, inpyrfluxam, isofetamid, pyrapropoyne, fluindapyr, fenpicoxamid, florylpicoxamid, acibenzolar-S-methyl, trinexepac-ethyl, fosetyl-aluminium, chlorothalonil, mancozeb, mandipropamid, oxathiapiprolin, fluazinam, fludioxonil, cyprodinil, metalaxyl-M, aminopyrifen, folpet, ipflufenoquin, quinofumelin, tebufloquin, tolprocarb, tricyclazole, pyroquilon, cyflufenamid, metrafenone, N'-[2-chloro-4-(2- fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine, N'-[4-(2-bromophenoxy)-5-chloro-2- methyl-phenyl]-N-ethyl-N-methyl-formamidine, N-(1-benzyl-1,3-dimethyl-butyl)-8-fluoro-quinoline-3- carboxamide, N-(1-benzyl-3,3,3-trifluoro-1-methyl-propyl)-8-fluoro-quinoline-3-carboxamide, N-(1- benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide, 1-(6,7-dimethylpyrazolo[1,5- a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(7- methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6- trifluoro-3,3-dimethyl-isoquinoline, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl- isoquinoline, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline, 6-chloro-4,4- difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline, N'-[5-bromo-2-methyl-6-(1-methyl-2- propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-chloro-2-methyl-6-(1-methyl-2- propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2- propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine, N-isopropyl-N’-[5-methoxy-2-methyl-4- (2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidineN-methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4- carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3- amine, methyl (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazol-1-yl]phenoxy]prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazol-1-yl)phenoxy]prop-2-enoate, methyl (Z)-2-[5-(3- isopropylpyrazol-1-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl- 5-(4-propyltriazol-2-yl)phenoxy]prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-[4- (trifluoromethyl)triazol-2-yl]phenoxy]prop-2-enoate, methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3- methoxy-prop-2-enoate, methyl (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, methyl (Z)-2-[5-(4-cyclohexylthiazol-2-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-2-[5- [4-(ethoxymethyl)thiazol-2-yl]-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-2-[5-(4- bromothiazol-2-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, and methyl (Z)-3-methoxy-2-[2- methyl-5-[5-(trifluoromethyl)thiazol-2-yl]phenoxy]prop-2-enoate. In another set of embodiments, component (B) is selected from the group consisting of: azoxystrobin, trifloxystrobin, pyraclostrobin, picoxystrobin, coumoxystrobin, metyltetraprole, cyproconazole, tebuconazole, difenoconazole, hexaconazole, propiconazole, fenhexamid, prothioconazole, mefentrifluconazole, prochloraz, fenpropidin, fenpropimorph, fluxapyroxad, fluopyram, isopyrazam, sedaxane, benzovindiflupyr, pydiflumetofen, isoflucypram, bixafen, penthiopyrad, inpyrfluxam, isofetamid, pyrapropoyne, fluindapyr, fenpicoxamid, florylpicoxamid, acibenzolar-S-methyl, trinexepac-ethyl, fosetyl-aluminium, chlorothalonil, mancozeb, mandipropamid, oxathiapiprolin, fluazinam, fludioxonil, cyprodinil, metalaxyl-M, aminopyrifen, folpet, ipflufenoquin, quinofumelin, tebufloquin, tolprocarb, tricyclazole, pyroquilon, cyflufenamid, metrafenone, N'-[2-chloro-4-(2- fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine, N'-[4-(2-bromophenoxy)-5-chloro-2- methyl-phenyl]-N-ethyl-N-methyl-formamidine, N-(1-benzyl-1,3-dimethyl-butyl)-8-fluoro-quinoline-3- carboxamide, N-(1-benzyl-3,3,3-trifluoro-1-methyl-propyl)-8-fluoro-quinoline-3-carboxamide, N-(1- benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide, 1-(6,7-dimethylpyrazolo[1,5- a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(7- methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6- trifluoro-3,3-dimethyl-isoquinoline, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl- isoquinoline, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline, 6-chloro-4,4- difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline, N'-[5-bromo-2-methyl-6-(1-methyl-2- propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-chloro-2-methyl-6-(1-methyl-2- propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2- propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine, N-isopropyl-N’-[5-methoxy-2-methyl-4- (2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidineN-methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4- carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3- amine, methyl (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazol-1-yl]phenoxy]prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazol-1-yl)phenoxy]prop-2-enoate, methyl (Z)-2-[5-(3- isopropylpyrazol-1-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl- 5-(4-propyltriazol-2-yl)phenoxy]prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-[4- (trifluoromethyl)triazol-2-yl]phenoxy]prop-2-enoate, methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3- methoxy-prop-2-enoate, methyl (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, methyl (Z)-2-[5-(4-cyclohexylthiazol-2-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-2-[5- [4-(ethoxymethyl)thiazol-2-yl]-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-2-[5-(4- bromothiazol-2-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5- [5-(trifluoromethyl)thiazol-2-yl]phenoxy]prop-2-enoate, TAEGRO®, Timorex GoldTM, and metarylpicoxamid. More preferably, component (B) is a compound selected from the group consisting of: azoxystrobin, trifloxystrobin, metyltetraprole, difenoconazole, hexaconazole, propiconazole, prothioconazole, mefentrifluconazole, fenpropidin, fenpropimorph, fluxapyroxad, fluopyram, isopyrazam, sedaxane, benzovindiflupyr, pydiflumetofen, isoflucypram, isofetamid, pyrapropoyne, fluindapyr, fenpicoxamid, florylpicoxamid, acibenzolar-S-methyl, chlorothalonil, mancozeb, mandipropamid, oxathiapiprolin, fluazinam, fludioxonil, cyprodinil, metalaxyl-M, aminopyrifen, folpet, ipflufenoquin, quinofumelin, tricyclazole, pyroquilon, cyflufenamid, metrafenone, N'-[2-chloro-4-(2- fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine N'-[4-(2-bromophenoxy)-5-chloro-2- methyl-phenyl]-N-ethyl-N-methyl-formamidine, N-(1-benzyl-1,3-dimethyl-butyl)-8-fluoro-quinoline-3- carboxamide, N-(1-benzyl-3,3,3-trifluoro-1-methyl-propyl)-8-fluoro-quinoline-3-carboxamide, N-(1- benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide, 1-(6,7-dimethylpyrazolo[1,5- a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(7- methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6- trifluoro-3,3-dimethyl-isoquinoline, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl- isoquinoline, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline, 6-chloro-4,4- difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline, N'-[5-bromo-2-methyl-6-(1-methyl-2- propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-chloro-2-methyl-6-(1-methyl-2- propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2- propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine, N-isopropyl-N’-[5-methoxy-2-methyl-4- (2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidine, N-methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4- carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3- amine, methyl (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazol-1-yl]phenoxy]prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazol-1-yl)phenoxy]prop-2-enoate, methyl (Z)-2-[5-(3- isopropylpyrazol-1-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl- 5-(4-propyltriazol-2-yl)phenoxy]prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-[4- (trifluoromethyl)triazol-2-yl]phenoxy]prop-2-enoate, methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3- methoxy-prop-2-enoate, methyl (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, methyl (Z)-2-[5-(4-cyclohexylthiazol-2-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-2-[5- [4-(ethoxymethyl)thiazol-2-yl]-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-2-[5-(4- bromothiazol-2-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, and methyl (Z)-3-methoxy-2-[2- methyl-5-[5-(trifluoromethyl)thiazol-2-yl]phenoxy]prop-2-enoate.
Figure imgf000021_0001
Figure imgf000022_0001
Figure imgf000023_0001
Figure imgf000024_0001
Figure imgf000025_0001
Figure imgf000026_0001
Figure imgf000027_0001
Figure imgf000028_0001
Figure imgf000029_0001
Figure imgf000030_0001
Figure imgf000031_0001
Figure imgf000032_0001
Figure imgf000033_0001
Figure imgf000034_0001
Figure imgf000035_0001
Figure imgf000036_0001
Figure imgf000037_0001
Figure imgf000038_0001
Figure imgf000039_0001
Figure imgf000040_0001
Figure imgf000041_0001
Figure imgf000042_0001
Figure imgf000043_0001
Figure imgf000044_0001
Figure imgf000045_0001
Figure imgf000046_0001
Figure imgf000047_0001
Figure imgf000048_0001
Figure imgf000049_0001
Figure imgf000050_0001
Figure imgf000051_0001
Figure imgf000052_0001
Figure imgf000053_0001
Figure imgf000054_0001
Figure imgf000055_0001
Figure imgf000056_0001
Figure imgf000057_0001
Figure imgf000058_0001
Figure imgf000059_0001
Figure imgf000060_0001
Figure imgf000061_0001
Figure imgf000062_0001
Figure imgf000063_0001
Figure imgf000064_0001
Figure imgf000065_0001
Figure imgf000066_0001
Figure imgf000067_0001
Figure imgf000068_0001
Figure imgf000069_0001
Figure imgf000070_0001
Figure imgf000071_0001
Figure imgf000072_0001
Figure imgf000073_0001
Figure imgf000074_0001
Figure imgf000075_0001
Figure imgf000076_0001
Figure imgf000077_0001
Figure imgf000078_0001
Figure imgf000079_0001
Figure imgf000080_0001
Figure imgf000081_0001
Figure imgf000082_0001
Figure imgf000083_0001
Figure imgf000084_0001
Figure imgf000085_0001
Figure imgf000086_0001
Figure imgf000087_0001
Figure imgf000088_0001
Figure imgf000089_0001
Figure imgf000090_0001
Figure imgf000091_0001
Figure imgf000092_0001
Figure imgf000093_0001
Figure imgf000094_0001
Figure imgf000095_0001
Figure imgf000096_0001
Figure imgf000097_0001
Figure imgf000098_0001
Figure imgf000099_0001
Figure imgf000100_0001
Figure imgf000101_0001
Figure imgf000102_0001
Figure imgf000103_0001
Figure imgf000104_0001
Figure imgf000105_0001
Figure imgf000106_0001
Figure imgf000107_0001
Figure imgf000108_0001
Figure imgf000109_0001
Figure imgf000110_0001
Figure imgf000111_0001
Figure imgf000112_0001
Figure imgf000113_0001
Figure imgf000114_0001
Figure imgf000115_0001
Figure imgf000116_0001
Figure imgf000117_0001
Figure imgf000118_0001
Figure imgf000119_0001
Figure imgf000120_0001
Figure imgf000121_0001
Figure imgf000122_0001
Figure imgf000123_0001
Figure imgf000124_0001
Figure imgf000125_0001
Figure imgf000126_0001
Figure imgf000127_0001
Figure imgf000128_0001
Figure imgf000129_0001
Figure imgf000130_0001
Figure imgf000131_0001
Figure imgf000132_0001
Figure imgf000133_0001
Figure imgf000134_0001
Figure imgf000135_0001
Figure imgf000136_0001
Figure imgf000137_0001
Figure imgf000138_0001
Figure imgf000139_0001
Figure imgf000140_0001
Figure imgf000141_0001
Figure imgf000142_0001
Figure imgf000143_0001
Figure imgf000144_0001
Figure imgf000145_0001
Figure imgf000146_0001
Figure imgf000147_0001
Figure imgf000148_0001
Figure imgf000149_0001
Figure imgf000150_0001
Figure imgf000151_0001
Figure imgf000152_0001
Figure imgf000153_0001
Figure imgf000154_0001
Figure imgf000155_0001
Figure imgf000156_0001
Figure imgf000157_0001
Figure imgf000158_0001
Figure imgf000159_0001
Figure imgf000160_0001
Figure imgf000161_0001
Figure imgf000162_0001
Figure imgf000163_0001
Figure imgf000164_0001
Figure imgf000165_0001
Figure imgf000166_0001
Figure imgf000167_0001
Figure imgf000168_0001
Figure imgf000169_0001
Figure imgf000170_0001
Figure imgf000171_0001
Figure imgf000172_0001
Figure imgf000173_0001
Figure imgf000174_0001
Figure imgf000175_0001
Figure imgf000176_0001
Figure imgf000177_0001
Figure imgf000178_0001
Figure imgf000179_0001
Figure imgf000180_0001
Figure imgf000181_0001
Figure imgf000182_0001
Figure imgf000183_0001
Figure imgf000184_0001
Figure imgf000185_0001
Figure imgf000186_0001
Figure imgf000187_0001
Figure imgf000188_0001
Figure imgf000189_0001
Figure imgf000190_0001
Figure imgf000191_0001
Figure imgf000192_0001
Figure imgf000193_0001
Figure imgf000194_0001
Figure imgf000195_0001
Figure imgf000196_0001
Figure imgf000197_0001
Figure imgf000198_0001
Figure imgf000199_0001
Figure imgf000200_0001
Figure imgf000201_0001
Figure imgf000202_0001
Figure imgf000203_0001
Figure imgf000204_0001
Figure imgf000205_0001
Figure imgf000206_0001
Figure imgf000207_0001
Figure imgf000208_0001
Figure imgf000209_0001
Figure imgf000210_0001
Figure imgf000211_0001
Figure imgf000212_0001
Figure imgf000213_0001
Figure imgf000214_0001
Figure imgf000215_0001
Figure imgf000216_0001
Figure imgf000217_0001
Figure imgf000218_0001
Figure imgf000219_0001
Example B10: Sclerotinia sclerotiorum / liquid culture (cottony rot) Mycelia fragments of a newly grown liquid culture of the fungus are directly mixed into nutrient broth (Vogel’s minimal media) containing 200µMol SHAM. After placing a (DMSO) solution of test compounds into a microtiter plate (96-well format) the nutrient broth containing the fungal material is added. The test plates are incubated at 24 °C and the inhibition of growth is determined photometrically 3-4 days after application. The following mixture compositions (A:B) at the reported concentration (in ppm) gave at least 80% disease control in this test when compared to the untreated control under the same conditions, which showed extensive disease development.
Figure imgf000219_0002
Figure imgf000220_0001
Figure imgf000221_0001
Figure imgf000222_0001
Figure imgf000223_0001
Figure imgf000224_0001
Figure imgf000225_0001
Figure imgf000226_0001
107-FF
Figure imgf000227_0001
Example B11: Blumeria graminis f. sp. tritici (Erysiphe graminis f. sp. tritici) / wheat / leaf disc preventative (Powdery mildew on wheat) Wheat leaf segments cv. Kanzler are placed on agar in a multiwell plate (24-well format) and sprayed with the formulated test compounds diluted in water. The leaf disks are inoculated by shaking powdery mildew infected plants above the test plates 1 day after application. The inoculated leaf disks are incubated at 20 °C and 60% rh under a light regime of 24 h darkness followed by 12 h light / 12 h darkness in a climate chamber and the activity of the compounds is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears on untreated check leaf segments (6 - 8 days after application). The following mixture compositions (A:B) at the reported concentration (in ppm) gave at least 80% disease control in this test when compared to the untreated control under the same conditions, which showed extensive disease development.
Figure imgf000227_0002
Figure imgf000228_0001
Figure imgf000229_0001
Figure imgf000230_0001
Figure imgf000231_0001
Figure imgf000232_0001
Figure imgf000233_0001
Figure imgf000234_0001
Figure imgf000235_0001
Figure imgf000236_0001
Figure imgf000237_0001
Figure imgf000238_0001
Figure imgf000239_0001
Figure imgf000240_0001
Example B12: Puccinia recondita f. sp. tritici / wheat / leaf disc preventative (Brown rust) Wheat leaf segments cv. Kanzler are placed on agar in multiwell plates (24-well format) and sprayed with the formulated test compounds diluted in water. The leaf disks are inoculated with a spore suspension of the fungus 1 day after application. The inoculated leaf segments are incubated at 19 °C and 75% rh under a light regime of 12 h light / 12 h darkness in a climate cabinet and the activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (7 - 9 days after application). The following mixture compositions (A:B) at the reported concentration (in ppm) gave at least 80% disease control in this test when compared to the untreated control under the same conditions, which showed extensive disease development.
Figure imgf000241_0001
Figure imgf000242_0001
Figure imgf000243_0001
Figure imgf000244_0001
Figure imgf000245_0001
Figure imgf000246_0001
Figure imgf000247_0001
Figure imgf000248_0001
Figure imgf000249_0001
Figure imgf000250_0001
Figure imgf000251_0001
Figure imgf000252_0001
Figure imgf000253_0001
107-FF
Figure imgf000254_0001
Example B13: Phakopsora pachyrhizi / soybean / preventative (soybean rust) Soybean leaf disks are placed on water agar in multiwell plates (24-well format) and sprayed with the formulated test compounds diluted in water. One day after application leaf discs are inoculated by spraying a spore suspension on the lower leaf surface. After an incubation period in a climate cabinet of 24-36 hours in darkness at 20 °C and 75% rh leaf disc are kept at 20 °C with 12 h light/day and 75% rh. The activity of the mixture composition is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf disks (12 - 14 days after application). The following mixture compositions (A:B) at the reported concentration (in ppm) gave at least 70% disease control in this test when compared to the untreated control under the same conditions, which showed extensive disease development.
Figure imgf000254_0002
Figure imgf000255_0001
Figure imgf000256_0001
Figure imgf000257_0001
Figure imgf000258_0001
Figure imgf000259_0001
Figure imgf000260_0001
Figure imgf000261_0001
Figure imgf000262_0001
Figure imgf000263_0001
Figure imgf000264_0001
Figure imgf000265_0001
Figure imgf000266_0001
Figure imgf000267_0001
Figure imgf000268_0001

Claims

CLAIMS: 1. A fungicidal composition comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is a compound of formula (I): wherein
Figure imgf000269_0001
X is N; Y is C-F or C-H; R1 is hydrogen, C1-C3alkyl, C1-C3alkoxy, C1-C3haloalkyl, C1-C3hydroxyalkyl, C1-C3alkoxyC1- C4alkyl, C3-C4cycloalkyl, C1-C2alkoxyC1-C2alkoxy, C1-C3alkoxycarbonylC1-C3alkyl, C1- C2alkoxycarbonyloxyC1-C2alkyl, C1-C2alkycarbonyloxyC1-C2alkyl, C3-C4alkynyloxy, C1-C3alkylsulfanyl, diethylamino, phenyl, benzyl, phenoxy, benzyloxyC1-C2alkyl, thienyl, or furanyl; R2 is C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkyl or HC(O)NH-; R3 is C3-C6cycloalkyl, wherein the cycloalkyl groups are optionally substituted with 1 or 2 groups represented by R4, or R3 is a 6- to 10-membered non-aromatic spirocyclic carbobi-cyclyl ring system; R4 is C1-C3alkyl; or a salt or an N-oxide thereof; and component (B) is a compound selected from the group consisting of: azoxystrobin, trifloxystrobin, pyraclostrobin, picoxystrobin, coumoxystrobin, metyltetraprole, cyproconazole, tebuconazole, difenoconazole, hexaconazole, propiconazole, fenhexamid, prothioconazole, mefentrifluconazole, prochloraz, fenpropidin, fenpropimorph, fluxapyroxad, fluopyram, isopyrazam, sedaxane, benzovindiflupyr, pydiflumetofen, isoflucypram, bixafen, penthiopyrad, inpyrfluxam, isofetamid, pyrapropoyne, fluindapyr, fenpicoxamid, florylpicoxamid, acibenzolar-S-methyl, trinexepac-ethyl, fosetyl-aluminium, chlorothalonil, mancozeb, mandipropamid, oxathiapiprolin, fluazinam, fludioxonil, cyprodinil, metalaxyl-M, aminopyrifen, folpet, ipflufenoquin, quinofumelin, tebufloquin, tolprocarb, tricyclazole, pyroquilon, cyflufenamid, metrafenone, N'-[2-chloro-4-(2- fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine, N'-[4-(2-bromophenoxy)-5-chloro-2- methyl-phenyl]-N-ethyl-N-methyl-formamidine, N-(1-benzyl-1,3-dimethyl-butyl)-8-fluoro-quinoline-3- carboxamide, N-(1-benzyl-3,3,3-trifluoro-1-methyl-propyl)-8-fluoro-quinoline-3-carboxamide, N-(1- benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide, 1-(6,7-dimethylpyrazolo[1,5- a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(7- methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6- trifluoro-3,3-dimethyl-isoquinoline, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl- isoquinoline, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline, 6-chloro-4,4- difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline, N'-[5-bromo-2-methyl-6-(1-methyl-2- propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-chloro-2-methyl-6-(1-methyl-2- propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2- propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine, N-isopropyl-N’-[5-methoxy-2-methyl-4- (2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidine, N-methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4- carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3- amine, methyl (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazol-1-yl]phenoxy]prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazol-1-yl)phenoxy]prop-2-enoate, methyl (Z)-2-[5-(3- isopropylpyrazol-1-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl- 5-(4-propyltriazol-2-yl)phenoxy]prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-[4- (trifluoromethyl)triazol-2-yl]phenoxy]prop-2-enoate, methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3- methoxy-prop-2-enoate, methyl (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, methyl (Z)-2-[5-(4-cyclohexylthiazol-2-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-2-[5- [4-(ethoxymethyl)thiazol-2-yl]-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-2-[5-(4- bromothiazol-2-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5- [5-(trifluoromethyl)thiazol-2-yl]phenoxy]prop-2-enoate, TAEGRO®, Timorex GoldTM, and metarylpicoxamid. 2. A fungicidal composition according claim 1, wherein component (A) is a compound selected from: [2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1-methyl-2- oxo-ethyl] acetate (compound X.01); [2-[[4-(cyclobutylcarbamoyl)-5-methyl-thiazol-2-yl]-(2,6-difluoro-4-pyridyl)amino]-1-methyl-2-oxo-ethyl] ethyl carbonate (compound X.02); [2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1-methyl-2- oxo-ethyl] methyl carbonate (compound X.03); [2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1-methyl-2- oxo-ethyl] ethyl carbonate (compound X.04); 2-[(2,6-difluoro-4-pyridyl)-(2-hydroxypropanoyl)amino]-5-methyl-N-spiro[3.4]octan-3-yl-thiazole-4- carboxamide (compound X.05); 2-[2-benzyloxypropanoyl-(2,6-difluoro-4-pyridyl)amino]-N-cyclobutyl-5-methyl-thiazole-4-carboxamide (compound X.06); N-cyclobutyl-2-[(2,6-difluoro-4-pyridyl)-(2-methoxypropanoyl)amino]-5-methyl-thiazole-4-carboxamide (compound X.07); [2-[(2,6-difluoro-4-pyridyl)-[4-[(2,2-dimethylcyclobutyl)carbamoyl]-5-methyl-thiazol-2-yl]amino]-2-oxo- ethyl] acetate (compound X.08); 2-[(2,6-difluoro-4-pyridyl)-(2-phenylacetyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.09); 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-5-methoxy-N-spiro[3.4]octan-3-yl-thiazole-4-carboxamide (compound X.10); 2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-5-methyl-N-spiro[3.4]octan-3-yl-thiazole-4- carboxamide (compound X.11); N-cyclobutyl-2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-5-methyl-thiazole-4-carboxamide (compound X.12); 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-N-cyclobutyl-5-methyl-thiazole-4-carboxamide (compound X.13); 2-[(2-benzyloxyacetyl)-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.14); 2-[(2,6-difluoro-4-pyridyl)-(2-ethoxyacetyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.15); 2-[diethylcarbamoyl-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.16); 2-[(2-chloroacetyl)-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.17); methyl 3-[(2,6-difluoro-4-pyridyl)-[4-[(2,2-dimethyl cyclobutyl)carbamoyl]-5-methyl-thiazol-2-yl]amino]-3- oxo-propanoate (compound X.18); 2-[(2,6-difluoro-4-pyridyl)-(furan-2-carbonyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.19); methyl 5-[(2,6-difluoro-4-pyridyl)-[4-[(2,2-dimethyl cyclobutyl)carbamoyl]-5-methyl-thiazol-2-yl] amino]- 5-oxo-pentanoate (compound X.20); 2-[(2,6-difluoro-4-pyridyl)-(3,3,3-trifluoropropanoyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl- thiazole-4-carboxamide (compound X.21); S-isopropyl N-(2,6-difluoro-4-pyridyl)-N-[4-[(2,2-dimethyl cyclobutyl)carbamoyl]-5-methyl-thiazol-2- yl]carbamothioate (compound X.22); methyl 4-[(2,6-difluoro-4-pyridyl)-[4-[(2,2-dimethyl cyclobutyl)carbamoyl]-5-methyl-thiazol-2-yl]amino]-4- oxo-butanoate (compound X.23); 2-[cyclopropane carbonyl-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole- 4-carboxamide (compound X.24); 2-[cyclopropane carbonyl-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole- 4-carboxamide (compound X.25); phenyl N-(2,6-difluoro-4-pyridyl)-N-[4-[(2,2-dimethylcyclobutyl)carbamoyl]-5-methyl-thiazol-2- yl]carbamate (compound X.26); 2-[(2,6-difluoro-4-pyridyl)-(2-fluoroacetyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.27); 2-methoxyethyl N-(2,6-difluoro-4-pyridyl)-N-[4-[(2,2-dimethylcyclobutyl)carbamoyl]-5-methyl-thiazol-2- yl]carbamate (compound X.28); 2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.29); ethyl N-(2,6-difluoro-4-pyridyl)-N-[4-[(2,2-dimethylcyclobutyl)carbamoyl]-5-methyl-thiazol-2- yl]carbamate (compound X.30); 2-[(2,6-difluoro-4-pyridyl)-(thiophene-2-carbonyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole- 4-carboxamide (compound X.31); methyl N-(2,6-difluoro-4-pyridyl)-N-[4-[(2,2-dimethylcyclobutyl)carbamoyl]-5-methyl-thiazol-2- yl]carbamate (compound X.32); 2-[(2,6-difluoro-4-pyridyl)-formyl-amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4-carboxamide (compound X.33); ethyl 2-[(2,6-difluoro-4-pyridyl)-[4-[(2,2-dimethylcyclobutyl)carbamoyl]-5-methyl-thiazol-2-yl]amino]-2- oxo-acetate (compound X.34); 2-[benzoyl-(2,6-difluoro-4-pyridyl) amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (compound X.35); 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4-carboxamide (compound X.36); 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-5-methyl-N-spiro[3.4] octan-3-yl-thiazole-4-carboxamide (compound X.37); and 2-[(2,6-difluoro-4-pyridyl)-(2-methylpropanoyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.38). 3. A fungicidal composition according to claim 1 or claim 2, wherein component (A) is selected from: [2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1-methyl-2- oxo-ethyl] acetate (compound X.01); [2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1-methyl-2- oxo-ethyl] ethyl carbonate (compound X.04); N-cyclobutyl-2-[(2,6-difluoro-4-pyridyl)-(2-methoxypropanoyl)amino]-5-methyl-thiazole-4-carboxamide (compound X.07); 2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-5-methyl-N-spiro[3.4]octan-3-yl-thiazole-4- carboxamide (compound X.11); N-cyclobutyl-2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-5-methyl-thiazole-4-carboxamide (compound X.12); 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-N-cyclobutyl-5-methyl-thiazole-4-carboxamide (compound X.13); 2-[(2-benzyloxyacetyl)-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.14); 2-[(2-chloroacetyl)-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.17); methyl 3-[(2,6-difluoro-4-pyridyl)-[4-[(2,2-dimethyl cyclobutyl)carbamoyl]-5-methyl-thiazol-2-yl]amino]-3- oxo-propanoate (compound X.18); 2-[(2,6-difluoro-4-pyridyl)-(furan-2-carbonyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.19); S-isopropyl N-(2,6-difluoro-4-pyridyl)-N-[4-[(2,2-dimethyl cyclobutyl)carbamoyl]-5-methyl-thiazol-2- yl]carbamothioate (compound X.22); 2-[cyclopropane carbonyl-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole- 4-carboxamide (compound X.24); phenyl N-(2,6-difluoro-4-pyridyl)-N-[4-[(2,2-dimethylcyclobutyl)carbamoyl]-5-methyl-thiazol-2- yl]carbamate (compound X.26); 2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.29); 2-[(2,6-difluoro-4-pyridyl)-(thiophene-2-carbonyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole- 4-carboxamide (compound X.31); 2-[(2,6-difluoro-4-pyridyl)-formyl-amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4-carboxamide (compound X.33); ethyl 2-[(2,6-difluoro-4-pyridyl)-[4-[(2,2-dimethylcyclobutyl)carbamoyl]-5-methyl-thiazol-2-yl]amino]-2- oxo-acetate (compound X.34); 2-[benzoyl-(2,6-difluoro-4-pyridyl) amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (compound X.35); 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4-carboxamide (compound X.36); 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-5-methyl-N-spiro[3.4] octan-3-yl-thiazole-4-carboxamide (compound X.37); and 2-[(2,6-difluoro-4-pyridyl)-(2-methylpropanoyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.38). 4. A fungicidal composition according to any one of claims 1 to 3, wherein component (A) is selected from: [2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1-methyl-2- oxo-ethyl] acetate (compound X.01); [2-[(2,6-difluoro-4-pyridyl)-[5-methyl-4-(spiro[3.4]octan-3-ylcarbamoyl)thiazol-2-yl]amino]-1-methyl-2- oxo-ethyl] ethyl carbonate (compound X.04); 2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-5-methyl-N-spiro[3.4]octan-3-yl-thiazole-4- carboxamide (compound X.11); N-cyclobutyl-2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-5-methyl-thiazole-4-carboxamide (compound X.12); 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-N-cyclobutyl-5-methyl-thiazole-4-carboxamide (compound X.13); 2-[(2-chloroacetyl)-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.17); methyl 3-[(2,6-difluoro-4-pyridyl)-[4-[(2,2-dimethyl cyclobutyl)carbamoyl]-5-methyl-thiazol-2-yl]amino]-3- oxo-propanoate (compound X.18); 2-[(2,6-difluoro-4-pyridyl)-(furan-2-carbonyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.19); 2-[cyclopropane carbonyl-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole- 4-carboxamide (compound X.24); 2-[(2,6-difluoro-4-pyridyl)-(2-methoxyacetyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.29); 2-[(2,6-difluoro-4-pyridyl)-formyl-amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4-carboxamide (compound X.33); ethyl 2-[(2,6-difluoro-4-pyridyl)-[4-[(2,2-dimethylcyclobutyl)carbamoyl]-5-methyl-thiazol-2-yl]amino]-2- oxo-acetate (compound X.34); 2-[benzoyl-(2,6-difluoro-4-pyridyl) amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (compound X.35); 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethyl cyclobutyl)-5-methyl-thiazole-4-carboxamide (compound X.36); 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-5-methyl-N-spiro[3.4] octan-3-yl-thiazole-4-carboxamide (compound X.37); and 2-[(2,6-difluoro-4-pyridyl)-(2-methylpropanoyl)amino]-N-(2,
2-dimethylcyclobutyl)-5-methyl-thiazole-4- carboxamide (compound X.38). 5. A fungicidal composition according to any one of claims 1 to 4, wherein component (B) is a compound selected from the group consisting of azoxystrobin, trifloxystrobin, metyltetraprole, difenoconazole, hexaconazole, propiconazole, prothioconazole, mefentrifluconazole, fenpropidin, fenpropimorph, fluxapyroxad, fluopyram, isopyrazam, sedaxane, benzovindiflupyr, pydiflumetofen, isoflucypram, isofetamid, pyrapropoyne, fluindapyr, fenpicoxamid, florylpicoxamid, acibenzolar-S- methyl, chlorothalonil, mancozeb, mandipropamid, oxathiapiprolin, fluazinam, fludioxonil, cyprodinil, metalaxyl-M, aminopyrifen, folpet, ipflufenoquin, quinofumelin, tricyclazole, pyroquilon, cyflufenamid, metrafenone, N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine N'-[4- (2-bromophenoxy)-5-chloro-2-methyl-phenyl]-N-ethyl-N-methyl-formamidine, N-(1-benzyl-1,3-dimethyl- butyl)-8-fluoro-quinoline-3-carboxamide, N-(1-benzyl-3,3,3-trifluoro-1-methyl-propyl)-8-fluoro-quinoline- 3-carboxamide, N-(1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide, 1-(6,7- dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, 4,4-difluoro-3,3-dimethyl- 1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6- trifluoro-3,
3-dimethyl-isoquinoline, 1-(4,5-dimethylbenzimidazol-1-yl)-4,
4,5-trifluoro-3,3-dimethyl- isoquinoline, 1-(4,
5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline, 6-chloro-4,4- difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline, N'-[5-bromo-2-methyl-6-(1-methyl-2- propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-chloro-2-methyl-6-(1-methyl-2- propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2- propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine, N-isopropyl-N’-[5-methoxy-2-methyl-4- (2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidine, N-methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4- carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3- amine, methyl (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazol-1-yl]phenoxy]prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazol-1-yl)phenoxy]prop-2-enoate, methyl (Z)-2-[5-(3- isopropylpyrazol-1-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl- 5-(4-propyltriazol-2-yl)phenoxy]prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-[4- (trifluoromethyl)triazol-2-yl]phenoxy]prop-2-enoate, methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3- methoxy-prop-2-enoate, methyl (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, methyl (Z)-2-[5-(4-cyclohexylthiazol-2-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-2-[5- [4-(ethoxymethyl)thiazol-2-yl]-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-2-[5-(4- bromothiazol-2-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5- [5-(trifluoromethyl)thiazol-2-yl]phenoxy]prop-2-enoate, TAEGRO®, Timorex GoldTM, and metarylpicoxamid.
6. A fungicidal composition according to any one of claims 1 to 5, wherein component (B) is a compound selected from the group consisting of azoxystrobin, trifloxystrobin, metyltetraprole, difenoconazole, hexaconazole, propiconazole, prothioconazole, mefentrifluconazole, fenpropidin, fenpropimorph, fluxapyroxad, fluopyram, isopyrazam, sedaxane, benzovindiflupyr, pydiflumetofen, isoflucypram, isofetamid, pyrapropoyne, fluindapyr, fenpicoxamid, florylpicoxamid, chlorothalonil, mancozeb, mandipropamid, oxathiapiprolin, fluazinam, fludioxonil, cyprodinil, metalaxyl-M, aminopyrifen, folpet, ipflufenoquin, quinofumelin, tricyclazole, pyroquilon, N-(1-benzyl-1,3-dimethyl- butyl)-8-fluoro-quinoline-3-carboxamide, N-(1-benzyl-3,3,3-trifluoro-1-methyl-propyl)-8-fluoro-quinoline- 3-carboxamide, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 1-(4,5- dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, and 1-(4,5-dimethylbenzimidazol- 1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline.
7. A fungicidal composition according to any one of claims 1 to 6, wherein the weight ratio of component (A) to component (B) is from 100:1 to 1:100.
8. A fungicidal composition according to any one of claims 1 to 7, wherein the weight ratio of component (A) to component (B) is from 20:1 to 1:40.
9. A fungicidal composition according to any one of claims 1 to 8, wherein the weight ratio of component (A) to component (B) is from 12:1 to 1:25.
10. A fungicidal composition according to any one of claims 1 to 9, wherein the weight ratio of component (A) to component (B) is from 5:1 and 1:15.
11. A fungicidal composition according to any one of claims 1 to 10, wherein the weight ratio of component (A) to component (B) is from 2:1 to 1:5.
12. A fungicidal composition according to any of claims 1 to 11, wherein the composition comprises one or more further pesticides selected from the group consisting of: a fungicide, selected from etridiazole, fluazinam, benzovindiflupyr, pydiflumetofen, benalaxyl, benalaxyl-M (kiralaxyl), furalaxyl, metalaxyl, metalaxyl-M (mefenoxam), dodicin, N'-(2,5-Dimethyl-4- phenoxy-phenyl)-N-ethyl-N-methyl-formamidine, N'-[4-(4,5-Dichloro-thiazol-2-yloxy)-2,5-dimethyl- phenyl]-N-ethyl-N-methyl-formamidine, N'-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl]oxy]-2,5- dimethyl-phenyl]-N-ethyl-N-methyl-formamidine, ethirimol, 3′-chloro-2-methoxy-N-[(3RS)-tetrahydro-2- oxofuran-3-yl]acet-2′,6′-xylidide (clozylacon), cyprodinil, mepanipyrim, pyrimethanil, dithianon, aureofungin, blasticidin-S, biphenyl, chloroneb, dicloran, hexachlorobenzene, quintozene, tecnazene, (TCNB), tolclofos-methyl, metrafenone, 2,6-dichloro-N-(4-trifluoromethylbenzyl)- benzamide, fluopicolide (flupicolide), tioxymid, flusulfamide, benomyl, carbendazim, carbendazim chlorhydrate, chlorfenazole, fuberidazole, thiabendazole, thiophanate-methyl, benthiavalicarb, chlobenthiazone, probenazole, acibenzolar, bethoxazin, pyriofenone (IKF-309), acibenzolar-S- methyl, pyribencarb (KIF-7767), butylamine, 3-iodo-2-propinyl n-butylcarbamate (IPBC), iodocarb (isopropanyl butylcarbamate), isopropanyl butylcarbamate (iodocarb), picarbutrazox, polycarbamate, propamocarb, tolprocarb, 3-(difluoromethyl)-N-(7-fluoro-1,1,3,3-tetramethyl-indan-4-yl)-1-methyl- pyrazole-4-carboxamide diclocymet, N-[(5-chloro-2-isopropyl-phenyl)methyl]-N-cyclopropyl-3- (difluoromethyl)-5-fluoro-1-methyl-pyrazole-4-carboxamide N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N- [(2-isopropylphenyl)methyl]-1-methyl-pyrazole-4-carboxamide carpropamid, chlorothalonil, flumorph, oxine-copper, cymoxanil, phenamacril, cyazofamid, flutianil, thicyofen, chlozolinate, iprodione, procymidone, vinclozolin, bupirimate, dinocton, dinopenton, dinobuton, dinocap, meptyldinocap, diphenylamine, phosdiphen, 2,6-dimethyl-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraone, azithiram, etem, ferbam, mancozeb, maneb, metam, metiram (polyram), metiram-zinc, nabam, propineb, thiram, vapam (metam sodium), zineb, ziram, dithioether, isoprothiolane, ethaboxam, fosetyl, fosetyl-aluminium (fosetyl-al), methyl bromide, methyl iodide, methyl isothiocyanate, cyclafuramid, fenfuram, validamycin, streptomycin, (2RS)-2-bromo-2-(bromomethyl)glutaronitrile (bromothalonil), dodine, doguadine, guazatine, iminoctadine, iminoctadine triacetate, 2,4-D, 2,4- DB, kasugamycin, dimethirimol, fenhexamid, hymexazole, hydroxyisoxazole imazalil, imazalil sulphate, oxpoconazole, pefurazoate, prochloraz, triflumizole, fenamidone, Bordeaux mixture, calcium polysulfide, copper acetate, copper carbonate, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper oxyquinolate, copper silicate, copper sulphate, copper tallate, cuprous oxide, sulphur, carbaryl, phthalide (fthalide), dingjunezuo (Jun Si Qi), oxathiapiprolin, fluoroimide, mandipropamid, KSF-1002, benzamorf, dimethomorph, fenpropimorph, tridemorph, dodemorph, diethofencarb, fentin acetate, fentin hydroxide, carboxin, oxycarboxin, drazoxolon, famoxadone, m-phenylphenol, p-phenylphenol, tribromophenol (TBP), 2-[2-[(7,8-difluoro-2-methyl-3- quinolyl)oxy]-6-fluoro-phenyl]propan-2-ol 2-[2-fluoro-6-[(8-fluoro-2-methyl-3- quinolyl)oxy]phenyl]propan-2-ol, cyflufenamid, ofurace, oxadixyl, flutolanil, mepronil, isofetamid, fenpiclonil, fludioxonil, pencycuron, edifenphos, iprobenfos, pyrazophos, phosphorus acids, tecloftalam, captafol, captan, ditalimfos, triforine, fenpropidin, piperalin, osthol, 1- methylcyclopropene, 4-CPA, chlormequat, clofencet, dichlorprop, dimethipin, endothal, ethephon, flumetralin, forchlorfenuron, gibberellic acid, gibberellins, hymexazol, maleic hydrazide, mepiquat, naphthalene acetamide, paclobutrazol, prohexadione, prohexadione-calcium, thidiazuron, tribufos (tributyl phosphorotrithioate), trinexapac, uniconazole, α-naphthalene acetic acid, polyoxin D (polyoxrim), BLAD, chitosan, fenoxanil, folpet, 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl- 2-(2,4,6-trichlorophenyl)ethyl]pyrazole-4-carboxamide, bixafen, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane, fenpyrazamine, diclomezine, pyrifenox, boscalid, fluopyram, diflumetorim, fenarimol, 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine ferimzone, dimetachlone (dimethaclone), pyroquilon, proquinazid, ethoxyquin, quinoxyfen, 4,4,5-trifluoro-3,3- dimethyl-1-(3-quinolyl)isoquinoline 4,4-difluoro-3,3-dimethyl-1-(3-quinolyl)isoquinoline 5-fluoro-3,3,4,4- tetramethyl-1-(3-quinolyl)isoquinoline 9-fluoro-2,2-dimethyl-5-(3-quinolyl)-3H-1,4-benzoxazepine, tebufloquin, oxolinic acid, chinomethionate (oxythioquinox, quinoxymethionate), spiroxamine, (E)-N- methyl-2- [2- (2, 5-dimethylphenoxymethyl) phenyl]-2-methoxy-iminoacetamide, (mandestrobin), azoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, pyriotrobin, fenamistrobin, flufenoxystrobin, fluoxastrobin, kresoxim-methyl, mandestrobin, metaminostrobin, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, triclopyricarb, trifloxystrobin, amisulbrom, dichlofluanid, tolylfluanid, but-3-ynyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)- phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate, dazomet, isotianil, tiadinil, thifluzamide, benthiazole (TCMTB), silthiofam, zoxamide, anilazine, tricyclazole, (.+-.)-cis-1-(4-chlorophenyl)-2- (1H-1,2,4-triazol-1-yl)-cycloheptanol (huanjunzuo), 1-(5-bromo-2-pyridyl)-2-(2,4-difluorophenyl)-1,1- difluoro-3-(1,2,4-triazol-1-yl)propan-2-ol 2-(1-tert-butyl)-1-(2-chlorophenyl)-3-(1,2,4-triazol-1-yl)-propan- 2-ol (TCDP), (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl- formamidine), azaconazole, bitertanol (biloxazol), bromuconazole, climbazole, cyproconazole, difenoconazole, dimetconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, mefentrifluconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triazoxide, triticonazole, 2- [[(1R,5S)-5-[(4-fluorophenyl)methyl]-1-hydroxy-2,2-dimethyl-cyclopentyl]methyl]-4H-1,2,4-triazole-3- thione 2-[[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl]-4H-1,2,4-triazole-3-thione, ametoctradin (imidium), iprovalicarb, valifenalate, 2-benzyl-4-chlorophenol (Chlorophene), allyl alcohol, azafenidin, benzalkonium chloride, chloropicrin, cresol, daracide, dichlorophen (dichlorophene), difenzoquat, dipyrithione, N-(2-p-chlorobenzoylethyl)-hexaminium chloride, NNF- 0721, octhilinone, oxasulfuron, Timorex GoldTM (plant extract comprising tea tree oil), propamidine and propionic acid; or an insecticide selected from abamectin, acephate, acetamiprid, amidoflumet (S- 1955), avermectin, azadirachtin, azinphos-methyl, bifenthrin, bifenazate, buprofezin, carbofuran, cartap, chlorantraniliprole (DPX-E2Y45), chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clothianidin, cyflumetofen, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, dieldrin, diflubenzuron, dimefluthrin, dimethoate, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, fenothiocarb, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flonicamid, flubendiamide, flucythrinate, tau-fluvalinate, flufenerim (UR-50701), flufenoxuron, fonophos, halofenozide, hexaflumuron, hydramethylnon, imidacloprid, indoxacarb, isofenphos, lufenuron, malathion, metaflumizone, metaldehyde, methamidophos, methidathion, methomyl, methoprene, methoxychlor, metofluthrin, monocrotophos, methoxyfenozide, nitenpyram, nithiazine, novaluron, noviflumuron (XDE-007), oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, profluthrin, pymetrozine, pyrafluprole, pyrethrin, pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen, rotenone, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen (BSN 2060), spirotetramat, sulprofos, tebufenozide, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, triazamate, trichlorfon and triflumuron; or a bactericide selected from streptomycin; or an acaricide selected from amitraz, chinomethionat, chlorobenzilate, cyenopyrafen, cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben and tebufenpyrad; or a biological agent selected from Bacillus thuringiensis, Bacillus thuringiensis delta endotoxin, baculovirus, and entomopathogenic bacteria, virus and fungi.
13. A fungicidal composition according to any one of claims 1 to 12, wherein the composition further comprises an agriculturally acceptable carrier and, optionally, a surfactant and/or formulation adjuvants.
14. A method of controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi, on useful plants or on propagation material thereof, which comprises applying to the useful plants, the locus thereof or propagation material thereof a fungicidal composition as defined in any one of claims 1 to 12.
15. A method according to claim 14, wherein the composition components (A) and (B) are applied in a sequential manner.
PCT/EP2021/064261 2020-06-03 2021-05-27 Fungicidal compositions WO2021244951A1 (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
AU2021284956A AU2021284956A1 (en) 2020-06-03 2021-05-27 Fungicidal compositions
EP21728570.9A EP4161277A1 (en) 2020-06-03 2021-05-27 Fungicidal compositions
US18/000,014 US20230270114A1 (en) 2020-06-03 2021-05-27 Fungicidal compositions
CR20220616A CR20220616A (en) 2020-06-03 2021-05-27 FUNGICIDE COMPOSITIONS
CN202180040155.6A CN115697063A (en) 2020-06-03 2021-05-27 Fungicidal compositions
CA3178082A CA3178082A1 (en) 2020-06-03 2021-05-27 Fungicidal compositions
MX2022015065A MX2022015065A (en) 2020-06-03 2021-05-27 Fungicidal compositions.
KR1020227044991A KR20230019126A (en) 2020-06-03 2021-05-27 fungicidal composition
JP2022574142A JP2023527894A (en) 2020-06-03 2021-05-27 Bactericidal composition
BR112022024658A BR112022024658A2 (en) 2020-06-03 2021-05-27 FUNGICIDAL COMPOSITIONS
IL298217A IL298217A (en) 2020-06-03 2021-05-27 Fungicidal compositions
CONC2022/0016858A CO2022016858A2 (en) 2020-06-03 2022-11-24 fungicidal compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP20178040.0 2020-06-03
EP20178040 2020-06-03

Publications (2)

Publication Number Publication Date
WO2021244951A1 true WO2021244951A1 (en) 2021-12-09
WO2021244951A9 WO2021244951A9 (en) 2022-01-13

Family

ID=70977432

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2021/064261 WO2021244951A1 (en) 2020-06-03 2021-05-27 Fungicidal compositions

Country Status (17)

Country Link
US (1) US20230270114A1 (en)
EP (1) EP4161277A1 (en)
JP (1) JP2023527894A (en)
KR (1) KR20230019126A (en)
CN (1) CN115697063A (en)
AR (1) AR122482A1 (en)
AU (1) AU2021284956A1 (en)
BR (1) BR112022024658A2 (en)
CA (1) CA3178082A1 (en)
CL (1) CL2022003410A1 (en)
CO (1) CO2022016858A2 (en)
CR (1) CR20220616A (en)
IL (1) IL298217A (en)
MX (1) MX2022015065A (en)
TW (1) TW202200014A (en)
UY (1) UY39241A (en)
WO (1) WO2021244951A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023099460A1 (en) * 2021-12-02 2023-06-08 Syngenta Crop Protection Ag Fungicidal compositions

Citations (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0367474A1 (en) 1988-11-01 1990-05-09 Mycogen Corporation Novel bacillus thuringiensis isolate denoted b.t. ps81gg, active against lepidopteran pests, and a gene encoding a lepidopteran-active toxin
EP0374753A2 (en) 1988-12-19 1990-06-27 American Cyanamid Company Insecticidal toxines, genes coding therefor, antibodies binding them, transgenic plant cells and plants expressing these toxines
WO1990013651A1 (en) 1989-05-09 1990-11-15 Imperial Chemical Industries Plc Bacterial genes
EP0401979A2 (en) 1989-05-18 1990-12-12 Mycogen Corporation Novel bacillus thuringiensis isolates active against lepidopteran pests, and genes encoding novel lepidopteran-active toxins
EP0427529A1 (en) 1989-11-07 1991-05-15 Pioneer Hi-Bred International, Inc. Larvicidal lectins and plant insect resistance based thereon
EP0451878A1 (en) 1985-01-18 1991-10-16 Plant Genetic Systems, N.V. Modifying plants by genetic engineering to combat or control insects
WO1993007278A1 (en) 1991-10-04 1993-04-15 Ciba-Geigy Ag Synthetic dna sequence having enhanced insecticidal activity in maize
WO1995034656A1 (en) 1994-06-10 1995-12-21 Ciba-Geigy Ag Novel bacillus thuringiensis genes coding toxins active against lepidopteran pests
WO2002015701A2 (en) 2000-08-25 2002-02-28 Syngenta Participations Ag Bacillus thuringiensis crystal protein hybrids
WO2003018810A2 (en) 2001-08-31 2003-03-06 Syngenta Participations Ag Modified cry3a toxins and nucleic acid sequences coding therefor
WO2003052073A2 (en) 2001-12-17 2003-06-26 Syngenta Participations Ag Novel corn event
WO2010012793A1 (en) 2008-08-01 2010-02-04 Bayer Cropscience Sa Fungicide aminothiazole derivatives
WO2011138281A2 (en) 2010-05-06 2011-11-10 Bayer Cropscience Ag Process for the preparation of dithiine tetracarboxydiimides
WO2014006945A1 (en) 2012-07-04 2014-01-09 アグロカネショウ株式会社 2-aminonicotinic acid ester derivative and bactericide containing same as active ingredient
WO2014095675A1 (en) 2012-12-19 2014-06-26 Bayer Cropscience Ag Difluoromethyl-nicotinic-indanyl carboxamides as fungicides
WO2015155075A1 (en) 2014-04-11 2015-10-15 Syngenta Participations Ag Fungicidal n'-[2-methyl-6-[2-alkoxy-ethoxy]-3-pyridyl]-n-alkyl-formamidine derivatives for use in agriculture
WO2016156085A1 (en) 2015-03-27 2016-10-06 Syngenta Participations Ag Microbiocidal heterobicyclic derivatives
WO2016156290A1 (en) 2015-04-02 2016-10-06 Bayer Cropscience Aktiengesellschaft Novel 5-substituted imidazole derivatives
WO2016202742A1 (en) 2015-06-15 2016-12-22 Bayer Cropscience Aktiengesellschaft Halogen-substituted phenoxyphenylamidines and the use thereof as fungicides
WO2016202688A1 (en) 2015-06-15 2016-12-22 Bayer Cropscience Aktiengesellschaft Halogen-substituted phenoxyphenylamidines and the use thereof as fungicides
WO2017025510A1 (en) 2015-08-12 2017-02-16 Syngenta Participations Ag Microbiocidal heterobicyclic derivatives
WO2017029179A1 (en) 2015-08-14 2017-02-23 Bayer Cropscience Aktiengesellschaft Triazole derivatives, intermediates thereof and their use as fungicides
WO2017055469A1 (en) 2015-10-02 2017-04-06 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
WO2017055473A1 (en) 2015-10-02 2017-04-06 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
WO2017093348A1 (en) 2015-12-02 2017-06-08 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
WO2017118689A1 (en) 2016-01-08 2017-07-13 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
WO2017153380A1 (en) 2016-03-10 2017-09-14 Syngenta Participations Ag Microbiocidal quinoline (thio)carboxamide derivatives
WO2017207362A1 (en) 2016-05-30 2017-12-07 Syngenta Participations Ag Microbiocidal thiazole derivatives
WO2017220485A1 (en) 2016-06-21 2017-12-28 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
WO2018065414A1 (en) 2016-10-06 2018-04-12 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
WO2018153707A1 (en) 2017-02-22 2018-08-30 Basf Se Crystalline forms of a strobilurin type compound for combating phytopathogenic fungi
WO2018158365A1 (en) 2017-03-03 2018-09-07 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
WO2018202428A1 (en) 2017-05-02 2018-11-08 Basf Se Fungicidal mixture comprising substituted 3-phenyl-5-(trifluoromethyl)-1,2,4-oxadiazoles
WO2018228896A1 (en) 2017-06-14 2018-12-20 Syngenta Participations Ag Fungicidal compositions
WO2019105933A1 (en) 2017-11-29 2019-06-06 Syngenta Participations Ag Microbiocidal thiazole derivatives
WO2019110427A1 (en) 2017-12-04 2019-06-13 Syngenta Participations Ag Microbiocidal phenylamidine derivatives
WO2020079111A1 (en) 2018-10-18 2020-04-23 Syngenta Crop Protection Ag Microbiocidal compounds
WO2020109511A1 (en) * 2018-11-30 2020-06-04 Syngenta Crop Protection Ag Microbiocidal 2-acylamino-thiazole-4-carboxamide derivatives

Patent Citations (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0451878A1 (en) 1985-01-18 1991-10-16 Plant Genetic Systems, N.V. Modifying plants by genetic engineering to combat or control insects
EP0367474A1 (en) 1988-11-01 1990-05-09 Mycogen Corporation Novel bacillus thuringiensis isolate denoted b.t. ps81gg, active against lepidopteran pests, and a gene encoding a lepidopteran-active toxin
EP0374753A2 (en) 1988-12-19 1990-06-27 American Cyanamid Company Insecticidal toxines, genes coding therefor, antibodies binding them, transgenic plant cells and plants expressing these toxines
WO1990013651A1 (en) 1989-05-09 1990-11-15 Imperial Chemical Industries Plc Bacterial genes
EP0401979A2 (en) 1989-05-18 1990-12-12 Mycogen Corporation Novel bacillus thuringiensis isolates active against lepidopteran pests, and genes encoding novel lepidopteran-active toxins
EP0427529A1 (en) 1989-11-07 1991-05-15 Pioneer Hi-Bred International, Inc. Larvicidal lectins and plant insect resistance based thereon
WO1993007278A1 (en) 1991-10-04 1993-04-15 Ciba-Geigy Ag Synthetic dna sequence having enhanced insecticidal activity in maize
WO1995034656A1 (en) 1994-06-10 1995-12-21 Ciba-Geigy Ag Novel bacillus thuringiensis genes coding toxins active against lepidopteran pests
WO2002015701A2 (en) 2000-08-25 2002-02-28 Syngenta Participations Ag Bacillus thuringiensis crystal protein hybrids
WO2003018810A2 (en) 2001-08-31 2003-03-06 Syngenta Participations Ag Modified cry3a toxins and nucleic acid sequences coding therefor
WO2003052073A2 (en) 2001-12-17 2003-06-26 Syngenta Participations Ag Novel corn event
WO2010012793A1 (en) 2008-08-01 2010-02-04 Bayer Cropscience Sa Fungicide aminothiazole derivatives
WO2011138281A2 (en) 2010-05-06 2011-11-10 Bayer Cropscience Ag Process for the preparation of dithiine tetracarboxydiimides
WO2014006945A1 (en) 2012-07-04 2014-01-09 アグロカネショウ株式会社 2-aminonicotinic acid ester derivative and bactericide containing same as active ingredient
WO2014095675A1 (en) 2012-12-19 2014-06-26 Bayer Cropscience Ag Difluoromethyl-nicotinic-indanyl carboxamides as fungicides
WO2015155075A1 (en) 2014-04-11 2015-10-15 Syngenta Participations Ag Fungicidal n'-[2-methyl-6-[2-alkoxy-ethoxy]-3-pyridyl]-n-alkyl-formamidine derivatives for use in agriculture
WO2016156085A1 (en) 2015-03-27 2016-10-06 Syngenta Participations Ag Microbiocidal heterobicyclic derivatives
WO2016156290A1 (en) 2015-04-02 2016-10-06 Bayer Cropscience Aktiengesellschaft Novel 5-substituted imidazole derivatives
WO2016202742A1 (en) 2015-06-15 2016-12-22 Bayer Cropscience Aktiengesellschaft Halogen-substituted phenoxyphenylamidines and the use thereof as fungicides
WO2016202688A1 (en) 2015-06-15 2016-12-22 Bayer Cropscience Aktiengesellschaft Halogen-substituted phenoxyphenylamidines and the use thereof as fungicides
WO2017025510A1 (en) 2015-08-12 2017-02-16 Syngenta Participations Ag Microbiocidal heterobicyclic derivatives
WO2017029179A1 (en) 2015-08-14 2017-02-23 Bayer Cropscience Aktiengesellschaft Triazole derivatives, intermediates thereof and their use as fungicides
WO2017055469A1 (en) 2015-10-02 2017-04-06 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
WO2017055473A1 (en) 2015-10-02 2017-04-06 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
WO2017093348A1 (en) 2015-12-02 2017-06-08 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
WO2017118689A1 (en) 2016-01-08 2017-07-13 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
WO2017153380A1 (en) 2016-03-10 2017-09-14 Syngenta Participations Ag Microbiocidal quinoline (thio)carboxamide derivatives
WO2017207362A1 (en) 2016-05-30 2017-12-07 Syngenta Participations Ag Microbiocidal thiazole derivatives
WO2017220485A1 (en) 2016-06-21 2017-12-28 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
WO2018065414A1 (en) 2016-10-06 2018-04-12 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
WO2018153707A1 (en) 2017-02-22 2018-08-30 Basf Se Crystalline forms of a strobilurin type compound for combating phytopathogenic fungi
WO2018158365A1 (en) 2017-03-03 2018-09-07 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
WO2018202428A1 (en) 2017-05-02 2018-11-08 Basf Se Fungicidal mixture comprising substituted 3-phenyl-5-(trifluoromethyl)-1,2,4-oxadiazoles
WO2018228896A1 (en) 2017-06-14 2018-12-20 Syngenta Participations Ag Fungicidal compositions
WO2019105933A1 (en) 2017-11-29 2019-06-06 Syngenta Participations Ag Microbiocidal thiazole derivatives
WO2019110427A1 (en) 2017-12-04 2019-06-13 Syngenta Participations Ag Microbiocidal phenylamidine derivatives
WO2020079111A1 (en) 2018-10-18 2020-04-23 Syngenta Crop Protection Ag Microbiocidal compounds
WO2020109511A1 (en) * 2018-11-30 2020-06-04 Syngenta Crop Protection Ag Microbiocidal 2-acylamino-thiazole-4-carboxamide derivatives

Non-Patent Citations (12)

* Cited by examiner, † Cited by third party
Title
COLBY, S.R.: "Calculating synergistic and antagonistic responses of herbicide combination", WEEDS, vol. 15, 1967, pages 20 - 22, XP001112961
COOLS ET AL., PLANT PATHOL, vol. 62, 2013, pages 36 - 42
FRAAIJE ET AL., PHYTOPATHOL, vol. 95, no. 8, 2005, pages 933 - 41
GISI ET AL., PEST MANAG SCI, vol. 56, 2000, pages 833 - 841
LUCAS, PESTIC OUTLOOK, vol. 14, no. 6, 2003, pages 268 - 70
MEUNIER ET AL., PEST MANAG SCI, vol. 75, 2019, pages 2107 - 2114
PASCHE ET AL.: "27", CROP PROTECTION, no. 3-5, 2008, pages 427 - 435
SCHMITZ HK ET AL., PEST MANAG SCI, vol. 70, 2014, pages 378 - 388
SEMAR ET AL., JOURNAL OF PLANT DISEASES AND PROTECTION, vol. 3, 2007, pages 117 - 119
SIEROTZKI ET AL., PEST MANAG SCI, vol. 63, no. 3, 2007, pages 225 - 233
SIEROTZKISCALLIET, PHYTOPATHOLOGY, vol. 103, no. 9, 2013, pages 880 - 887
SIMÕES ET AL., J PLANT DIS PROT, vol. 125, 2018, pages 21 - 2

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023099460A1 (en) * 2021-12-02 2023-06-08 Syngenta Crop Protection Ag Fungicidal compositions

Also Published As

Publication number Publication date
IL298217A (en) 2023-01-01
UY39241A (en) 2021-12-31
CL2022003410A1 (en) 2023-05-26
WO2021244951A9 (en) 2022-01-13
AR122482A1 (en) 2022-09-14
US20230270114A1 (en) 2023-08-31
CO2022016858A2 (en) 2022-12-09
EP4161277A1 (en) 2023-04-12
KR20230019126A (en) 2023-02-07
JP2023527894A (en) 2023-06-30
CR20220616A (en) 2023-03-20
CA3178082A1 (en) 2021-12-09
BR112022024658A2 (en) 2022-12-27
AU2021284956A1 (en) 2022-12-08
TW202200014A (en) 2022-01-01
MX2022015065A (en) 2023-01-11
CN115697063A (en) 2023-02-03

Similar Documents

Publication Publication Date Title
EP3361870B1 (en) Fungicidal compositions
AR112097A1 (en) FUNGICIDE COMPOSITIONS
DK2263455T3 (en) Composition against harmful organisms and method for control of harmful organisms
US10111433B2 (en) Fungicidal compositions
EP2928298B1 (en) Oil-based pesticidal suspension
KR101819258B1 (en) Water-based pesticidal suspension
KR20100120215A (en) Plant disease control agent
JP2020525501A5 (en)
WO2018060140A1 (en) Microbiocidal benzoxaboroles derivatives
JP2017535254A (en) Rice seed treatment method
US20180244699A1 (en) 1-hydroxy-3h-2,1-benzoxaborole derivatives and their use as microbiocides
AU2017388342B2 (en) Solid pest control composition comprising cyclaniliprole or salt thereof
AU2021284956A1 (en) Fungicidal compositions
AU2017230471A1 (en) Method for enhancing plant disease controlling effect of isofetamid and method for controlling plant disease
WO2015162268A1 (en) Microbiocidal imidazole derivatives
JP2024516883A (en) Herbicide/safener combinations based on safeners of the class of substituted [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acids and their salts
EP4255185A1 (en) Fungicidal compositions
CN113840533A (en) Active compound combinations
US20210267194A1 (en) Seed treatment method
JPWO2020208096A5 (en)
WO2016204160A1 (en) Soybean disease control composition and soybean disease control method
KR101801427B1 (en) Copulation disruption agent for sap-sucking pests
CA3127986A1 (en) Agricultural chemical preparation containing difenoconazole, and method for stabilizing said agricultural chemical preparation
EP2451275B2 (en) Agricultural or horticultural fungicide composition and its use for controlling plant pathogens
EP4295683A1 (en) Agrochemical formulations comprising crystalline form a of 4-[(6-chloro-3-pyridylmethyl)(2,2-difluoroethyl)amino]furan-2(5h)-one

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 21728570

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 3178082

Country of ref document: CA

ENP Entry into the national phase

Ref document number: 2022574142

Country of ref document: JP

Kind code of ref document: A

ENP Entry into the national phase

Ref document number: 2021284956

Country of ref document: AU

Date of ref document: 20210527

Kind code of ref document: A

REG Reference to national code

Ref country code: BR

Ref legal event code: B01A

Ref document number: 112022024658

Country of ref document: BR

ENP Entry into the national phase

Ref document number: 20227044991

Country of ref document: KR

Kind code of ref document: A

ENP Entry into the national phase

Ref document number: 112022024658

Country of ref document: BR

Kind code of ref document: A2

Effective date: 20221201

ENP Entry into the national phase

Ref document number: 16127

Country of ref document: GE

WWE Wipo information: entry into national phase

Ref document number: 16127/1

Country of ref document: GE

NENP Non-entry into the national phase

Ref country code: DE

ENP Entry into the national phase

Ref document number: 2021728570

Country of ref document: EP

Effective date: 20230103